Weekend Guide: Things to Do in Santa Cruz & Monterey, September 18-20
It is the third full weekend of September and both counties are showing off. The Santa Cruz County Fair fills Watsonville with carnival lights, hometown headliners, and drone shows after dark. Down in Monterey County, the Great Carmel Sandcastle Contest takes over Carmel Beach, the PURE Insurance Championship brings PGA TOUR Champions legends to Pebble Beach, and GRIDLIFE turns Laguna Seca into a three-day motorsport and music festival. Saturday morning, the whole community turns out for the 42nd California Coastal Cleanup Day. There is a county fair, a wine and brew festival in the mountains, a free street music festival downtown, and championship golf by the sea all in one weekend. Here is how to make the most of every minute.
I have called Santa Cruz County home for more than 50 years, and this is exactly the kind of weekend that makes me love this place. Grab your people, pick a couple of these, and go. The events are the stars, and I am just here to help you find them. Let me plan it with you.
Friday, September 18
Santa Cruz County Fair, Opening Weekend
Noon to 11:00 PM | Santa Cruz County Fairgrounds, 2601 East Lake Avenue, Watsonville
The 2026 Santa Cruz County Fair runs Wednesday through Sunday with the theme “Apple Pies and Starry Skies.” Friday is the calm, uncrowded night to go: wander the exhibits and livestock barns, ride the carnival classics, load up on fair food, then settle in for headliner Andy Vargas, the Watsonville native and longtime lead vocalist for Carlos Santana, at 7:30 PM. The Electric Sky Drone Show lights up the Pajaro Valley sky after the music. Friday is my favorite night for a leisurely lap through the whole fair. I will be there.
GRIDLIFE Laguna Festival
Friday to Sunday | WeatherTech Raceway Laguna Seca, 1021 Monterey-Salinas Highway, Salinas
The season finale of the GRIDLIFE calendar returns to one of the most famous racetracks in the world. Expect the final rounds of the Touring Cup and the NOS Energy TrackBattle Time Attack, high-energy drifting, live music, tuner car displays, and an open-air arcade. Whether you come for the legendary Corkscrew or the car culture, this is a three-day celebration of everything on four wheels.
PURE Insurance Championship Impacting First Tee
Friday to Sunday | Pebble Beach Golf Links and Poppy Hills, Pebble Beach
PGA TOUR Champions legends are paired with junior golfers from the First Tee program for one of the most heartwarming tournaments on the calendar. Walking the fairways of Pebble Beach while the Monterey Bay crashes against the cliffs below is a spectator experience unlike any other. The junior players sharing the course with the legends is what makes this weekend genuinely special.
Night Owl 2026
Friday evening | Pacific Grove Museum of Natural History, Pacific Grove
The museum's annual grown-up fundraiser, themed “Curiosities After Dark,” brings live music, interactive science, and local flavor to the Monterey Peninsula. A fun, quirky night out that supports a great local institution.
Carmel Art Association 8x10 Exhibition Opens
Opens Friday | Carmel-by-the-Sea
The beloved annual show where hundreds of local artists contribute original 8x10 works, all at one accessible price point. A fantastic way to buy original art, meet artists, and kick off the fall arts season in Carmel.
Borchard Farms Pumpkin Patch Opens
Opens Friday, daily through October 31 | Watsonville area
The first pumpkin patch of the season opens this weekend. Giant pumpkins, a five-acre corn maze, farm animals, and all the fall energy you could want. A perfect preview of October for families.
Saturday, September 19
42nd California Coastal Cleanup Day
9:00 AM to noon | Sites across Santa Cruz and Monterey Counties
Save Our Shores coordinates dozens of beach and watershed cleanup sites across Santa Cruz County, with more along the Monterey coast at Asilomar, Carmel City Beach, Del Monte Beach, Fort Ord Dunes, and Garrapata. Gloves and bags are provided, and it is a wonderful family activity. Start your Saturday giving back to the coastline we all love. I will be out there.
34th Annual Aloha Outrigger Races
8:00 AM to 2:00 PM | Santa Cruz Wharf
Outrigger canoe teams race around the wharf while hula performances keep the aloha energy going on shore. Novice-friendly and free to watch from the wharf, it is a lively, distinctly Santa Cruz Saturday morning on the water.
63rd Annual Great Carmel Sandcastle Contest
7:00 AM to noon | Carmel Beach, south of 10th Avenue
Carmel's signature beach tradition returns with the theme “It Never Gets Old: Carmel at 110.” Sand sculptors start building at 7:00 AM, judging is at 11:00 AM, and awards follow around noon. Free to watch, endlessly photogenic, and the best people-watching on the Peninsula.
Boardwalk PRIDE
Starts 11:00 AM | Santa Cruz Beach Boardwalk, 400 Beach Street
The Boardwalk celebrates the LGBTQ+ community with free live entertainment, giveaways, info booths, and all the rides and games you could want. A joyful day of color and community on the beach, perfect for the whole crew.
Bonny Doon Art, Wine and Brew Festival
2:00 to 7:00 PM | Crest Ranch, 12200 Empire Grade, Bonny Doon
The 23rd annual festival returns to the Santa Cruz Mountains with tastings from local wineries and breweries, an artist and craft vendor marketplace, a Mountain Makerspace with artist-led workshops, food trucks, and live music. It is a 21-and-over fundraiser for the Bonny Doon School arts and academics programs. Tickets sell out, so grab yours online.
Santa Cruz Farmers Markets, Saturday
Westside Santa Cruz, 9:00 AM to 1:00 PM | Scotts Valley, 8:00 AM to noon | Aptos at Cabrillo College, 8:00 AM to noon
Peak harvest Saturday. Heirloom tomatoes, late-summer stone fruit, and the first apples and pears of the season at all three markets. Grab a picnic lunch here before the fair or the beach.
Open Studios Art Tour of Monterey County, Day 1
11:00 AM to 5:00 PM | Artists across Monterey County, free
The second weekend of the county's open studios tour, with artists welcoming you into their working spaces. Pick up the free guide, hop between studios, and meet the people behind the work. Venture Gallery in Monterey is an easy starting point.
Alternative Zen Blues Trial
7:00 to 10:00 PM | Abbott Square Market, 118 Cooper Street, downtown Santa Cruz
Free outdoor rock, blues, and funk in the heart of downtown. Grab dinner from the market's food vendors and settle in under the string lights for a relaxed Saturday evening.
Crooner Ed at the Stanton Center
7:30 PM | Monterey History and Art Museum, Stanton Center, Monterey
A nostalgic night of classic crooner standards in a beautiful waterfront venue, with tickets around $28. A polished date-night option in Old Monterey.
American Heart Walk
9:00 AM | Monterey Bay Coastal Recreation Trail, starting across from the Naval Postgraduate School, Monterey
A free community walk along the coast to support heart health. Bring the family, get some steps in, and support a good cause with beautiful views.
More Saturday Highlights
Scottish Day at Ben Lomond County Park, 1:00 PM
Highland games, music, and community in the redwoods.
Hispanic and Latine Festival at Woodhouse Blending and Brewing, noon, 119 Madrone Street, Santa Cruz
An afternoon of music, food, and community in Santa Cruz.
Santa Cruz Guitar Company 50th Anniversary Concert at the Rio Theatre, evening
An all-star evening honoring five decades of handmade guitars in Santa Cruz.
Sunday, September 20
Santa Cruz County Fair, Final Day
10:00 AM to 10:00 PM | Santa Cruz County Fairgrounds, Watsonville
The last day of the fair. Livestock auctions, final carnival rides, last servings of fair food, and the Electric Sky Drone Show after the evening's entertainment. If you have not made it yet, this is your last chance.
Cedar Street Music Festival
Noon to 6:00 PM | Cedar Street between Maple and Laurel, downtown Santa Cruz
A free street festival presented by the City of Santa Cruz, with live local artists filling downtown with music all afternoon. Wander the closed street, grab a bite nearby, and enjoy a relaxed Sunday.
Open Studios Art Tour of Monterey County, Day 2
11:00 AM to 5:00 PM | Artists across Monterey County, free
A second full day of studio visits across the county. If you missed Saturday, Sunday is your chance to meet the artists and see where the work happens.
Live Oak Farmers Market
9:00 AM to 1:00 PM | 15th Avenue and East Cliff Drive, Santa Cruz
Sunday morning market on the east side, a relaxed neighborhood favorite with local produce and artisan vendors. Grab your haul and walk a block to Seabright Beach for a September picnic.
PURE Insurance Championship, Final Round
All day | Pebble Beach Golf Links, Pebble Beach
The championship is decided on the back nine at Pebble Beach with the Monterey Bay as the backdrop. The best day to walk the course and watch the drama unfold.
GRIDLIFE Laguna Festival, Final Day
All day | WeatherTech Raceway Laguna Seca, Salinas
Championship rounds and final drifting sessions close out the festival. If you have a weekend pass, Sunday is the payoff.
California Surfing Day
All day | Marina State Beach and breaks across both counties
Visit California's statewide celebration of surf culture falls this Sunday. September glass and smaller crowds make it a lovely day to paddle out, or to watch from the sand at Marina State Beach.
All Weekend: Outdoor Adventures and Year-Round Favorites
Kayaking Elkhorn Slough
Daily | Moss Landing, about 20 minutes south of Santa Cruz
September is spectacular on Elkhorn Slough. Sea otters float among the eelgrass, harbor seals haul out on the mudflats, and migratory shorebirds begin their southward passage. The slough is calm and protected, ideal for beginners and kids. Early morning is the best time to spot otters at their most active.
Hiking the Redwoods
Daily | Henry Cowell Redwoods State Park, Felton; The Forest of Nisene Marks, Aptos; Fall Creek Unit, Felton
Three world-class redwood parks within 15 minutes of each other. Henry Cowell has the easy old-growth loop through trees that were already centuries old when California became a state. Nisene Marks offers more than 30 miles of trails, and Fall Creek is quieter, following the creek through dappled September light. Mild temperatures make this the ideal hiking weekend.
Monterey Bay Coastal Recreation Trail
18 miles from Castroville to Pacific Grove
Walk, run, or bike along one of the most scenic paved trails on the California coast. The stretch between Monterey and Pacific Grove passes Cannery Row, the Monterey Bay Aquarium, and Lovers Point with panoramic views of the bay. September brings thinner crowds and mild temperatures.
Whale Watching in Monterey Bay
Daily departures | Fisherman's Wharf, Monterey, and Santa Cruz Harbor
Humpback whales are actively feeding in Monterey Bay through the fall, building their reserves before the long migration south. September offers some of the best whale watching of the year. Bring a warm jacket, even on warm days, because the bay breeze runs cool offshore.
Monterey Bay Aquarium
Open daily | 886 Cannery Row, Monterey
The kelp forest, the Open Sea exhibit with schools of tuna and sea turtles, the touch pools, and the mesmerizing jellyfish gallery. September crowds are thinner than summer. Book ahead online.
Food and Drink Highlights
Bonny Doon Art, Wine and Brew Festival
Saturday, 2:00 to 7:00 PM | Crest Ranch, Bonny Doon
The tasting event of the weekend. Local wineries and breweries pour samples, food trucks keep everyone fed, and live music plays into the evening, all under the redwoods. Tickets sell out, so grab yours online ahead of time.
Santa Cruz County Fair Food
This is the fair food weekend of the year. Corn dogs, funnel cakes, kettle corn, turkey legs, cotton candy, caramel apples, and everything on a stick. The apple pie theme is everywhere this year, so do not skip it.
Westside Santa Cruz Wine Tasting
The Westside wine trail is minutes from the Saturday farmers market. Birichino Winery at 204 Church Street and Bottle Jack Winery at 1088 La Madrona Drive both have tasting rooms open on Saturday. If you are heading toward Scotts Valley, Inversion Wines at 75 Mt. Hermon Road and Saison Cellar at 222 Mt. Hermon Road are worth the trip.
Santa Cruz Breweries
Humble Sea Brewing at 820 Swift Street and Santa Cruz Mountain Brewing at 402 Ingalls Street are Saturday favorites. Woodhouse Blending and Brewing at 119 Madrone Street hosts the Hispanic and Latine Festival on Saturday at noon, a great way to pair beer with community.
Abbott Square Market
118 Cooper Street, Downtown Santa Cruz
Open all weekend with a rotating lineup of food vendors. The outdoor plaza with string lights is a perfect spot for a casual September dinner, and Saturday night brings free live music.
Arts and Culture
Open Studios Art Tour of Monterey County
Saturday and Sunday, 11:00 AM to 5:00 PM, free
Artists across Monterey County open their studios for the second weekend of the tour. Venture Gallery in Monterey is an easy starting point to plan your route.
Carmel Art Association 8x10 Exhibition
Opens Friday | Carmel-by-the-Sea
Hundreds of original small works from local artists, all at one accessible price. A signature way to start the fall arts season.
Night Owl 2026
Friday evening | Pacific Grove Museum of Natural History
The annual “Curiosities After Dark” fundraiser blends live music and interactive science for a playful night out in Pacific Grove.
Santa Cruz Shakespeare
Performances through early October | DeLaveaga Park, Santa Cruz
The summer season is still going under the redwoods, with Jason Robert Brown's “The Last Five Years” and Noël Coward's “Private Lives” both on stage. A talk-back for The Last Five Years happens Saturday. Check santacruzshakespeare.org for times and tickets.
Rio Theatre
Saturday evening | 1205 Soquel Avenue, Santa Cruz
The Santa Cruz Guitar Company 50th Anniversary Concert celebrates five decades of handmade guitars with a night of live music at the historic Rio.
Notable Community News and New Openings
The Santa Cruz County Fair is here through Sunday. The 2026 theme “Apple Pies and Starry Skies” captures exactly what makes this fair special. Andy Vargas, the Watsonville native and longtime Santana vocalist, performs Friday. James Durbin performs Saturday. A drone show lights up the sky each night.
Boardwalk PRIDE is Saturday, September 19. The Santa Cruz Beach Boardwalk celebrates the LGBTQ+ community with free live entertainment, giveaways, and info booths starting at 11:00 AM.
The Looff Carousel marks its 115th anniversary this September. One of the oldest carousels in the country and a beloved Boardwalk icon, worth a ride while you are there.
Borchard Farms Pumpkin Patch opens Friday. The first pumpkin patch of the season, with giant pumpkins, a five-acre corn maze, and farm animals. It runs daily through October 31.
Santa Cruz Guitar Company turns 50. The local luthier celebrates with an anniversary concert at the Rio Theatre on Saturday night.
Coastal Cleanup Day is Saturday, September 19. The 42nd annual statewide cleanup runs from 9:00 AM to noon. Sites across both counties, with gloves and bags provided. Bring the family and help keep our coastline beautiful.
Shareable Social Captions
Planning to post about your weekend? Here are some ready-to-copy captions for Instagram and Facebook, written as if I am sharing my own plans with friends.
County fair weekend is finally here. The Santa Cruz County Fair is on through Sunday with carnival lights, drone shows after dark, and hometown heroes Andy Vargas from Santana on Friday and James Durbin on Saturday. Saturday morning I am joining Coastal Cleanup Day at the beach. Who wants to come help me make a difference, then hit the fair for a corn dog? 🍎 ⭐ #SantaCruzEvents #SantaCruzCountyFair #ThingsToDoSantaCruz #WeekendInSantaCruz #SantaCruzLife
One weekend, both counties. The county fair in Watsonville, the Great Carmel Sandcastle Contest on the beach, PGA legends and junior golfers at Pebble Beach, race cars through the Corkscrew at Laguna Seca, and a wine and brew festival in the Santa Cruz Mountains. This is why I will never stop loving this place. There is always something happening. 🏁 🏖️ #SantaCruzEvents #WeekendInSantaCruz #ThingsToDoSantaCruz #MontereyBay #SantaCruzLife
The family plan is locked in. Coastal Cleanup Day Saturday morning to teach the kids about caring for our beaches. Boardwalk PRIDE for rides and color in the afternoon. The County Fair at night for animals, rides, and the drone show. Sunday, the Great Carmel Sandcastle Contest in the morning and the Live Oak farmers market for a beach picnic. Pack the crew and go. 🏖️ 🌈 #FamilyFunSantaCruz #SantaCruzEvents #WeekendInSantaCruz #ThingsToDoSantaCruz
Art and culture lovers, this is your weekend. Open Studios Art Tour opens studios across Monterey County. The Carmel Art Association 8x10 show opens Friday with original art at one accessible price. Santa Cruz Shakespeare has shows under the redwoods. And the Cedar Street Music Festival fills downtown Santa Cruz with free live music on Sunday. See you out there. 🎨 🎭 #SantaCruzEvents #ThingsToDoSantaCruz #OpenStudiosMonterey #SantaCruzLife
My Saturday, start to finish: Coastal Cleanup Day in the morning, the Westside farmers market for apples and flowers, the Bonny Doon Art, Wine and Brew Festival in the mountains from 2 to 7, then free music at Abbott Square Market. If you see me out there, come say hi. Talk soon. 🍷 🎶 #SantaCruzEvents #ThingsToDoSantaCruz #WeekendInSantaCruz #SantaCruzLife #MontereyBay
Enjoy the weekend, everyone. Whether you are riding the Ferris wheel at the County Fair, cleaning up the beach for Coastal Cleanup Day, watching drivers attack the Corkscrew at Laguna Seca, or collecting a stack of 8x10 art in Carmel, I hope this weekend gives you moments you will carry into the fall. If you are thinking about buying or selling a home in Santa Cruz or Monterey County, I would love to hear from you. Call me at (831) 247-5719 or visit the contact page. I want you to make informed decisions, and I love helping people find their place in this beautiful corner of California.
Talk soon.
Kieron Bery, REALTOR® with Century 21 Masters
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